Those are two amazing questions that deserve volumes of their own.
Here are a couple of books I found helpful.
In answer to the question of what is the right thing to do or not do, check out M. Scott Peck, in “The Road Less Traveled.” He wrote that when we suffer over the decisions we make for our children, they will know that they have value, regardless of whether they like our decision or not. I thought that was a wonderful idea to believe in as I tried to navigate the often treacherous waters of being a parent.
In answer to the question of how a boy becomes a man and what that means, I would look at Sam Keen’s “Fire in the Belly.” He has a great quote:
“There are two questions a man must ask himself: The first is ‘Where am I going?’ and the second is ‘Who will go with me?’
If you ever get these questions in the wrong order you are in trouble.”
For most men, our idenity is tied in to what we do, not our relationships. It takes a long time to travel on this path before we gain enough experience (both success and failure) to get to a point where we ask who we really are and what is meaningful.
I remember listening to a talk about initiation, the rituals created by societies that mark the beginning of manhood. In some African tribes, the initiation process can be potentially fatal. The speaker said that the tribe depended on the uncles to help the boys go through these painful challenges. The parents were too close and would either be too soft or too hard on the boy, which could hurt their ability to overcome the challenges of the initiation ritual. The uncles were family, so they cared about helping the boys succeed, but they were detached enough in their relationship that they wouldn’t compromise the ritual and the lessons that had to be learned.
The closest things we have in modern day America are sports and the military. Neither are perfect in creating a well rounded man, but in combination with your guidance about learning respect and how you model being a good person, they may help fill in some of the gaps that you feel you can’t provide.
Just being aware of these issues gives you a leg up on helping him become the man he needs to become.